


Leather and Lace

by DRHPaints



Series: Kinky Bill One Shots [2]
Category: Bill Hader - Fandom, Bill Hader RPF, US Comedians RPF
Genre: Anal Fingering, Anal Sex, Bill Hader - Freeform, Established Relationship, Explicit Language, Explicit Sexual Content, FTM, Lingerie, M/M, Makeup, Other, Restraints, Smut, Strap-Ons, Transmasculine
Language: English
Status: Completed
Published: 2020-08-13
Updated: 2020-08-13
Packaged: 2021-03-06 06:13:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,428
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25878730
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Bill agrees to dress up in lingerie for his transmasc lover, Ian, who then ties him up and tops him.
Relationships: Bill Hader/Original Transmasc Character
Series: Kinky Bill One Shots [2]
Series URL: https://archiveofourown.org/series/1877902
Kudos: 2





	Leather and Lace

**Author's Note:**

> I apologize to anyone subscribing to my stuff. I realized I wasn’t posting this collection of one shots in the most effective manner, so I’m sorry if you’re getting notifications for things you already read.

Turning the page, Ian scanned down and sighed. He’d given it three chapters, but this writer’s style was painfully dense and he was growing annoyed. There was, however, something about one of the characters that had given him an idea.  
“Hey Bill?” He lay next to him in bed re-reading George Saunders’ _Lincoln in the Bardo_ , one of his favorites.   
Marking his place with his thumb, he turned to Ian, “Hmm?”  
“Would you ever let me…dress you up?” Ian bit the corner of his lip, raising an eyebrow.  
Bill gathered his prominent eyebrows. “What, you mean like help me pick out a new suit?”  
“Uhh…no,” Ian scratched his chin, looking into Bill’s deep blue eyes with a grin. “Like…like lingerie.”  
Bill burst into giggles, face scrunching up until his left eye closed completely, top teeth extending over the bottom ones. “What? _No!_ Why?” He held up his hands and shook his head.  
Shrugging his shoulder, Ian leaned into him, drawing his nose across Bill’s neck. “Aw, come on. You would be so sexy…” Exhaling slowly against his skin, Ian dragged his teeth lightly across Bill’s sensitive flesh and felt him shiver beneath him.  
“You…you think so?” Bill murmured, turning his body into him.   
Ian tiptoed his hand over Bill’s thigh and between his legs. “ _Definitely_.”  
**

Grinning, Ian found himself shopping, having effectively convinced Bill the night before. Making his selections, he proceeded to the register, and as he drove home he caught himself gripping the steering wheel tight in anticipation.   
Ian stood outside of the bedroom for over ten minutes. “Are you sure you don’t need any help?” He called through the door. It had been years since he’d worn any of those things, but he knew firsthand how tricky they could be, especially for a first timer.  
“No…no I got it,” came Bill’s slightly nasal voice. “I just…” he paused, and Ian leaned into the door. “I feel silly…”  
“Aw, honey, come on,” Ian insisted, placing a hand on the door. “I bet you look great. Just let me see, okay?”  
After a moment the door opened just a sliver, exposing Bill’s bent over face. Pulling back the door he revealed himself to be wearing a flat black lace bra with matching low rise panties, fishnet thigh highs, complete with garter, and his large feet were shoved into four inch black satin pumps. Bill held his hands in front of himself timidly, shifting his weight from one leg to the other.  
Ian’s mouth dropped open. The combination of the soft and sexy lingerie with his expansive shoulders, strong arms, and little pudgy belly was exhilarating. And the fact that the tiny lace panties barely restrained his massive cock made Ian throb internally.  
But Bill looked at him, shaking his head. “I knew it, I _knew_ it, this was stupid,” he reached behind himself to undo the bra and Ian rushed forward to stop him.   
“Bill, _Bill_ , no!” Ian shook his head. “I mean… _damn_ Bill…” he was having trouble finding words, so he just ran his hands over Bill’s waist, his chest, his arms. “Fuck Bill.”  
Grinning, Bill ran his tongue over his teeth. “You really like it?”  
“Honey…” Ian looked him up and down. “You are _so damn beautiful_.” Bill blushed and brought a hand to his cheek, which made Ian want to tear into him like a rabid dog, but he restrained himself. “Could I…would you be okay putting on a little makeup? Maybe?”  
Looking off to the side, Bill pursed his lips. “Yeah…I guess that would be okay.”  
Ian nodded and went to their closet. Buried deep in the back was a box of his things from before his transition. Even before, he was never the kind of person who wore a lot of makeup, but he did have a handful of items, and as he fished out the tiny makeup bag he smiled.  
“Okay, sit down,” Bill took a seat on the bed, looking up at him coquettishly through his eyelashes, and Ian had to fight to steady himself before instructing Bill to look up so he could apply a bit of eyeliner. Retrieving a tube of blood red lipstick, he dragged it over Bill’s curvaceous pink lips, instructing him to smear them together. Finishing it off by telling Bill to close his eyes so he could brush the lightest of pinks over his eyelids, Bill looked up at him and Ian couldn’t stop smiling.  
“ _Fuck_ , Bill you’re so damn pretty,” he caressed his sharp jaw, rubbing a thumb over his prominent cheekbone, a shudder running through him when Bill closed his eyes and tipped his head to nestle against his palm.  
Ian’s hand trailed down, hooking his finger underneath the strap of Bill’s bra before leaning down and getting close to his face.  
“ _Do you want me to fuck you, baby_?” He whispered, breathing against those blood red lips.  
Nodding, Bill dragged his nails over Ian’s forearm. “ _Yes. Yes, please fuck me_.”  
Cupping his hand under Bill’s chin, Ian directed him to stand, pulling him into his mouth and firmly grabbing his ass, before pushing him back on the bed, laying him down and straddling him. Ian lifted Bill’s arms above his head, kissing him feverishly and grinding against him through the fabric of his jeans as he pinned him to the mattress.  
“Bill,” Ian breathed, pulling away. “I want to tie you up.”  
Bill looked at him, lips swollen, lipstick smeared, eyes heavy with lust. “ _Yes_.”  
Ian hopped off and pulled the box from under their bed, retrieving the four leather straps. Starting with his ankles, he snatched them to each corner, knowing Bill liked it when he pushed him around a little. Ian noticed his raging erection, head peeking out of the black lace panties, no longer able to be restrained, and he tingled. Sharply dragging Bill’s wrist to the headboard, Bill’s red mouth dropped open in anticipation.  
When he was properly restrained, Ian rummaged around their sex box again, disrobing and stepping into the harness, selecting one of the larger strap-ons in their collection. Tossing a bottle of lube on the bed, Ian kneeled between Bill’s legs, running his hands over his sculpted thighs before leaning over to catch his mouth in a kiss.  
Grinding against him, Ian grazed his fingers over Bill’s swollen purple cock, provoking a mewling whine from deep in his chest, and despite his limited range of motion, he desperately tried to gain friction against Ian’s body.   
Flipping open the tube of lube, Ian applied some to his fingers, and pushing Bill’s lace panties to the side he rubbed against the tight muscle of his entrance before sliding in with two fingers and crooking upwards, Bill’s back arching as he tickled his prostate. Ian pulsed inside him, digging further, until Bill was straining against the leather straps and shaking his head back and forth, makeup smudged eyes shut tight in frustration.  
“ _Ian, fuck me. Just fuck me, please_ ,” Bill pleaded. Ian applied lube to the dildo, and more to Bill’s tight muscle, before circling against him and inching inside. Gasping, head pressed back against the mattress, Bill accepted him greedily, and once he was fully sheathed Ian reached up and pulled down Bill’s panties to release his dripping cock, rubbing the glistening head with the ball of his thumb as he stroked into him. Getting to his knees, Ian lifted Bill’s ass and began pounding upwards, a high whine escaping Bill every time he hit his prostate, tugging his thick cock, finding himself distracted by just how achingly gorgeous Bill looked, head thrown back, red mouth agape, blue eyes fluttering in ecstasy, pale skin flushed and dark hair plastered against his forehead.  
“ _Fuck, fuck, Ian, I’m gonna cum_ ,” Bill whimpered, the long line of his neck exposed as he thrashed against his bonds, thighs rocking side to side as he desperately tried to drive Ian deeper inside himself. Shuddering, Bill’s cum shot across his abdomen and chest, pouring over Ian’s knuckles and staining the lace of the bra. Reaching between his own thighs, Ian polished himself off in less than a minute just looking at Bill’s freshly fucked form splayed out before him, gasping and wet around his own fingers.  
Climbing up, Ian laid next to Bill, kissing his stubbled cheek and running his fingers through his dark chest hair.   
“Thank you, lovely,” Ian whispered against his skin, holding him close.  
Turning to him, still restrained, Bill kissed him with a lipstick-smudged mouth. “The pleasure was all mine.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this, please leave a comment or come say hi on tumblr at fandomtransmandom :-)


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